EP0206606B1 - Flüssiger Entwickler für elektrostatische latente Bilder - Google Patents

Flüssiger Entwickler für elektrostatische latente Bilder Download PDF

Info

Publication number
EP0206606B1
EP0206606B1 EP86304361A EP86304361A EP0206606B1 EP 0206606 B1 EP0206606 B1 EP 0206606B1 EP 86304361 A EP86304361 A EP 86304361A EP 86304361 A EP86304361 A EP 86304361A EP 0206606 B1 EP0206606 B1 EP 0206606B1
Authority
EP
European Patent Office
Prior art keywords
liquid developer
solvent
set forth
weight
alkyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP86304361A
Other languages
English (en)
French (fr)
Other versions
EP0206606A2 (de
EP0206606A3 (en
Inventor
Tsuneyuki Kondo
Yasuhiro Sato
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Toray Industries Inc
Original Assignee
Toray Industries Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Toray Industries Inc filed Critical Toray Industries Inc
Publication of EP0206606A2 publication Critical patent/EP0206606A2/de
Publication of EP0206606A3 publication Critical patent/EP0206606A3/en
Application granted granted Critical
Publication of EP0206606B1 publication Critical patent/EP0206606B1/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G9/00—Developers
    • G03G9/08—Developers with toner particles
    • G03G9/12—Developers with toner particles in liquid developer mixtures
    • G03G9/13—Developers with toner particles in liquid developer mixtures characterised by polymer components
    • G03G9/133—Graft-or block polymers
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
    • Y10S430/001—Electric or magnetic imagery, e.g., xerography, electrography, magnetography, etc. Process, composition, or product
    • Y10S430/105—Polymer in developer

Definitions

  • the present invention relates to a liquid developer used for developing an electrostatic latent image formed by electrophotography or electrostatography.
  • liquid developers comprise an electrical resistive carrier liquid having a high electrical resistance and a low dielectric constant, such as an aliphatic hydrocarbon solvent, and toner particles dispersed in the carrier liquid.
  • the toner particles contain a binder, a coloring agent and other additives.
  • a natural or synthetic resin as a binder, a pigment or dye as a coloring agent, and a metallic soap or another dispersant as an additive are mixed and kneaded intimately with the carrier liquid to prepare a concentrate toner having a non-volatile matter content of about 1-20%, which concentrate toner is then diluted to about 0.1-5% in terms of a non-volatile matter content to obtain a liquid developer.
  • the toner particles in the liquid toner be dispersed stably while maintaining a certain particle size in a mutually bonded state of the binder and the coloring agent.
  • the resin component of the binder gradually dissolves out from the toner particles into the carrier liquid, thus resulting in gradual deterioration in point of fusing and charge of the toner particles.
  • the resulting toner particles are not uniform and are coarse, resulting in that the dispersion stability is poor and there occur aggregation and sedimentation of the toner particles during storage.
  • a liquid developer for electrostatic latent image using such polymer may afford a good print characteristic at the beginning of development, but has been disadvantageous in that as the number of prints increases, the concentration of the printed image area is reduced markedly to the extent that it is no longer recovered even by adding a concentrate toner to the developer, and thus such a good print as that obtained at the beginning of development is no longer obtainable.
  • electrostatic paper of A-1 size was printed continuously at a percent image area of 5%, the concentration of the printed image area decreased rapidly at 100 m printing and it became extremely low at 500 m printing, from which it did not recover even by the addition of a concentrate toner.
  • the "percent image area of 5%” means that the area of the printed portion is 5% relative to the area of the paper used, and the "100 m printing” and “500 m printing” indicate time points at which, in the printing of an oblong A-1 size paper at a predetermined percent image area, the total paper length became 100 m and 500 m, respectively.
  • liquid toner comprising a solvent system containing a polymeric material having a moiety soluble in the solvent system and another moiety insoluble therein is described in GB-A-1352067.
  • the present invention relates to a liquid developer for electrostatic latent image, comprising the components (a), (b) and (c), as set out in Claim 1, which are dispersed in an electrical resistive aliphatic hydrocarbon solvent.
  • the electrical resistive aliphatic hydrocarbon solvent used as a dispersion medium, or a carrier liquid, for the non-gel copolymer, coloring agent and dispersant has an electrical resistivity not smaller than 109 ⁇ cm, a dielectric constant not larger than 3 and a boiling point in the range of 68° to 250°C.
  • Examples are hexane, octane, nonane, decane, undecane and dodecane, as well as such organic solvents as "ISOPAR" H, G, L and M which are available commercially (products of EXXON Chemical Inc.). Particularly, solvents boiling in the range of 100° to 200°C, e.g. "ISOPAR" G and H, are preferred.
  • the liquid developer of the present invention is characterized by containing a non-gel copolymer which consists essentially of a specific copolymer segment ("soluble copolymer segment”) soluble in the electrical resistive aliphatic hydrocarbon solvent and a specific polymer segment ("insoluble polymer segment”) insoluble in the said solvent and which as the whole of its molecules is insoluble in the said solvent.
  • the soluble copolymer segment is for stabilizing the dispersion of the copolymer used in the invention and it comprises as main monomer components (i) one or more monomers (hereinafter referred to sometimes as "alkyl (meth)acrylate”) selected from alkyl acrylates and alkyl methacrylates and (ii) one or more monomers selected from cycloalkyl methacrylates and aralkyl methacrylates.
  • alkyl (meth)acrylate monomers selected from alkyl acrylates and alkyl methacrylates
  • a copolymer segment containing alkyl (meth)acrylate and cycloalkyl methacrylate as main components is preferred.
  • the alkyl group of the alkyl (meth)acrylate used as a component of the soluble copolymer segment usually has 3 to 20, preferably 4 to 18, carbon atoms.
  • alkyl (meth)acrylates are such as butyl, isobutyl, tertiary butyl, 2-ethylhexyl, octyl, isononyl, decyl, lauryl, dodecyl and stearyl acrylate or methacrylate.
  • the cycloalkyl group of the cycloalkyl methacrylate is usually in the form of a six-membered ring of 6 to 8 carbon atoms, preferably cyclohexyl. As the most preferred example is mentioned cyclohexyl methacrylate.
  • benzyl methacrylate is the most preferred.
  • a polymerization product of alkyl (meth)acrylate has low glass transition point, so a too high content thereof results in stickiness of the print obtained. If stearyl (meth)acrylate is used in order to avoid such inconvenience, the resulting image will have "blur".
  • the present invention by using the cycloalkyl methacrylate and/or aralkyl methacrylate as a comonomer, there can be formed a stickiness- and blur-free image even in an increased amount of the soluble copolymer segment.
  • the soluble copolymer segment is a copolymer of (i) at least one alkyl (meth)acrylate and (ii) at least one cycloalkyl methacrylate or aralkyl methacrylate.
  • another vinyl compound (iii) may also be a comonomer, e.g. versatic vinyl "VeoVa 10" (a product of Shell Kagaku Kabushiki Kaisha).
  • VeoVa 10 a product of Shell Kagaku Kabushiki Kaisha.
  • an organic mercaptan as a polymerization modifier because the dispersion stability of the insoluble polymer segment will be improved.
  • the organic mercaptan there is used a higher alkylmercaptan having an alkyl group of 7 or more carbon atoms, preferably 8-20 carbon atoms, generally employed as a polymerization modifier.
  • Preferred examples are n-octylmercaptan, n-dodecylmercaptan, t-dodecylmercaptan and n-octadecylmercaptan.
  • azobisalkylnitrile having an alkyl group of 3 to 6 carbon atoms.
  • azobisisobutyronitrile is preferred.
  • the insoluble polymer segment is a polymer segment containing vinyl acetate as a main component. It may be a homopolymer of vinyl acetate, or may be a copolymer of vinyl acetate and one or more of other vinyl monomers such as alkyl acrylates, alkyl methacrylates, cycloalkyl acrylates, cycloalkyl methacrylates, aralkyl acrylates and aralkyl methacrylates.
  • the vinyl acetate content of the polymer segment containing vinyl acetate as a main component is preferably 50 to 100 wt.%, preferably 65 to 100 wt.%.
  • the alkyl group of the alkyl acrylate or alkyl methacrylate just referred to above has usually 1 to 20 carbon atoms, preferably 1 to 18, carbon atoms.
  • Preferred examples of alkyl acrylate or alkyl methacrylate are such as methyl, ethyl, 2-hydroxyethyl, isobutyl, octyl, stearyl and isononyl acrylate or methacrylate.
  • alkyl includes hydroxyalkyl.
  • the cycloalkyl group of the cycloalkyl methacrylate is usually in the form of a six-membered ring of 6 to 8 carbon atoms, preferably cyclohexyl.
  • the most preferred examples of the cycloalkyl methacrylate is cyclohexyl methacrylate.
  • benzyl methacrylate is the most preferred.
  • diacyl peroxides are usually employable. Preferred examples are benzoyl peroxide, lauroyl peroxide and p-chlorobenzoyl peroxide.
  • the copolymer used in the invention may be prepared using, for example, the foregoing aliphatic hydrocarbon solvent as a reaction solvent.
  • a two-step process in which first the monomers for constituting the soluble copolymer segment are added into the reaction solvent and polymerization is allowed to take place and then in this state the monomer or monomers for constituting the insoluble polymer segment are added and polymerized.
  • the molecular weight of the copolymer used in the invention differs depending on the kind and combination of monomers used, but preferably it is adjusted to a value in the range of 5,000 to 50,000, more preferably 8,000 to 20,000.
  • the copolymer used in the invention as the entirety of its molecules, be insoluble in the solvent and not gel-like. Since the liquid developer of the present invention is constituted by such a specific copolymer, even when the toner concentration in the developer decreases, the concentration of the printed image area can be maintained constant by replenishing a concentrate toner. And its life can be made extremely long.
  • the ratio of the soluble copolymer segment to the insoluble polymer segment differs depending on the combination of monomers used, but preferably the proportion of the soluble copolymer segment is in the range of 25 to 60 wt.%, more preferably 30 to 45 wt.%, of the whole of the copolymer used in the invention. Within this range, the particle size of the insoluble polymer segment is presumed to become smaller, thus permitting a sufficient bond between the coloring agent and the soluble polymer segment as well as enhanced dispersion stability of the developer. Also in point of uniformity of toner particles as well as transfer and cleaning, the above range is preferred.
  • the method of bonding those segments is not specially limited.
  • a form of a graft copolymer comprising the soluble copolymer segment with the insoluble polymer segment is preferred.
  • the coloring agent used in the present invention is not specially limited.
  • Various known coloring agents for this type of toner are employable. Examples are carbon black, organic and inorganic pigments, and dyes.
  • coloring agents for black there are mentioned carbon black, Spirit Black, Aniline Black (C.I. Pigment Black 1), and metal calcined pigments.
  • carbon black is furnace black, acetylene black and channel black.
  • coloring agents for cyan there are mentioned Dianisidine Blue (C.I. Pigment Blue 25), Phthalocyanine Blue (C.I. Pigment Blue 15), Victoria Pure Blue Lake (C.I. Pigment Blue 1), and Alkali Blue Toner (C.I. Pigment Blue 18).
  • coloring agents for magenta there are mentioned azo-lake pigments such as Barium Red 28 (C.I. Pigment Red 48:1), Calcium Red 2B (C.I. Pigment Red 48:2), Strontium Red (C.I. Pigment Red 48:3), Manganese Red 2B (C.I. Pigment Red 48:4), Barium Lithol Red (C.I. Pigment Red 49:1), Calcium Red 52 (C.I. Pigment Red 52:1), Lake Red C (C.I. Pigment Red 53:1), Brilliant Carmine 6B (C.I. Pigment Red 57:1), BON Maroon L-58 (C.I. Pigment Red 58:4), Brilliant Carmine 3B (C.I.
  • Pigment Red 60:1), and Brilliant Scarlet G (C.I. Pigment Red 64:1); lake pigments from basic dyes, e.g. Rhodamine 6G Lake (C.I. Pigment Red 81); and quinacridone pigments, e.g. Quinacridone Magenta (C.I. Pigment Red 122).
  • coloring agents for yellow there are mentioned insoluble monoazo pigments such as Fast Yellow G (C.I. Pigment Yellow 1) and Fast Yellow 10G (C.I. Pigment Yellow 3), as well as insoluble disazo pigments such as Disazo Yellow AAA (C.I. Pigment Yellow 12), Disazo Yellow AAMX (C.I. Pigment Yellow 13), Disazo Yellow AAOT (C.I. Pigment Yellow 14), and Disazo Yellow AAOA (C.I. Pigment Yellow 17).
  • insoluble monoazo pigments such as Fast Yellow G (C.I. Pigment Yellow 1) and Fast Yellow 10G (C.I. Pigment Yellow 3
  • insoluble disazo pigments such as Disazo Yellow AAA (C.I. Pigment Yellow 12), Disazo Yellow AAMX (C.I. Pigment Yellow 13), Disazo Yellow AAOT (C.I. Pigment Yellow 14), and Disazo Yellow AAOA (C.I. Pigment Yellow 17).
  • the dispersant used in the present invention greatly contributes to the improvement of toner dispersion stability, preservability and printing performance in cooperation with the specific copolymer used as a binder in the invention.
  • the dispersant is not specially limited if only it can improve the dispersion stability and preservability of toner.
  • Preferred examples are metallic salts of naphthenic, octylic and stearic acids.
  • constituent metals of the metallic salts Group II and IV metals in the Periodic Table as well as transition metals, such as Li, Ca, Ba, Zr, Mn, Co, Ni, Cu, Zn, Cd, Al and Pt, are effective.
  • Aluminum stearate is particularly preferred.
  • Oligomers, preferably trimer, of aluminum oxide stearate are also preferred, examples of which are "OLIEPE AOS” (a product of Hope Seiyaku K.K.) and "OLIEPE AOO" (a product of the same company).
  • the liquid developer of the present invention can be prepared by milling a dispersion of the copolymer prepared in the above manner, the coloring agent such as pigment or dye and the dispersant, intimately by means of a ball mill or a sand mill to obtain a concentrate toner having a non-volatile matter content of about 1-20 wt.% and then diluting the concentrate toner with the foregoing aliphatic hydrocarbon solvent so that the non-volatile matter content becomes about 1-5 wt.%.
  • the toner particle size is not specially limited, but preferably it is in the range of 0.3 to 1.5 ⁇ m in terms of an average particle diameter.
  • the liquid developer of the present invention is effective in developing an electrostatic latent image obtained by electrophotography or electrostatography.
  • electrophotography to which is applied the liquid developer of the present invention there are mentioned wet type copier and printer, while as examples of electrostatography to which is applied the same liquid developer, there are mentioned facsimile and electrostatic plotter.
  • the liquid developer for electrostatic latent image of the present invention is particularly suitable for multicolor printing because it has an extremely superior trapping property.
  • multicolor printing printing is usually performed using developers for three primary colors, i.e. cyan, magenta and yellow, as well as black, successively in an appropriate order.
  • developers for three primary colors i.e. cyan, magenta and yellow, as well as black
  • a latent image of a second color is formed and developed, and these operations are repeated successively.
  • conventional developers however, the multicolor overlapping effect is difficult to attain because of inferior trapping property, that is, because of difficulty of developing the second and the following colors.
  • the liquid developer of the present invention has a good trapping property which is attained by using the specific copolymer as a binder. Besides, the transparency is also good. Consequently, a number of colors can be superimposed upon one another and underlying colors can be reflected, thus affording a clear and reproducible multicolor printing effect. Multicolor printing can be effected, for example, by the use of a color electrostatic plotter.
  • the developer of the present invention is preferably applied to a color electrostatic plotter in which electrostatic latent images corresponding to each color are applied to an electrostatic paper and printing is made by a single apparatus in black, cyan, magenta and yellow colors successively.
  • the liquid developer for electrostatic latent image of the present invention contains the specific copolymer as a binder, so even if the toner concentration in the developer decreases, the concentration of the printed image area can be maintained constant by replenishing a concentrate toner. Thus, an extremely outstanding effect can be attained.
  • liquid developer of the present invention is superior in trapping property and transparency, it is possible to obtain a clear image of good reproducibility in multicolor printing.
  • component (a) i.e. binder
  • component (a) i.e. binder
  • ISOPAR G an aliphatic solvent
  • ISOPAR G a product of EXXON Chemical Inc.
  • a mixed solution of 140 parts 2-ethylhexyl methacrylate, 60 parts benzyl methacrylate, 4 parts dodecylmercaptan and 2 parts azobisisobutyronitrile was dripped for about one hour, and thereafter a polymerization reaction was allowed to take place for another one hour under stirring and heating at 90°C.
  • Example 7 The electrostatic paper which had been developed using the developer obtained in Example 1 was rewound and then developed using the developer obtained in Example 7. As a result, a good printing performance like that in Example 7 was obtained and a good blue was reproduced at an overlapped portion of cyan and magenta. This electrostatic paper was again rewound and then developed using the developer prepared in Example 8. As a result, a good printing performance like that in Example 8 was obtained; besides, a good green was reproduced at an overlapped portion of cyan and yellow, and a good red reproduced at a magenta-yellow overlapped portion.
  • Example 11 The same procedure as in Example 11 was repeated except that first the yellow in Example 8 was developed, then the magenta in Example 7 was developed and thereafter the cyan in Example 1 was developed. In all the cases printing was effected to a satisfactory extent and there were reproduced good green, blue and red at overlapped portions.
  • a developer was prepared in the same way as in Example 1 except that the polymer solution obtained in Production Example 7 was used. Using 2 l of the developer, development was done in the same manner as in Example 1; as a result, a clear image was obtained. The concentration of the printed image area of cyan of the image was 1.38.
  • the concentration of the printed image area of cyan was 0.96.
  • the concentrate toner was added to the developer followed by printing; as a result, the concentration of the printed image area recovered to 1.34.
  • Example 2 Using the same developer as in Example 1, there was made development by means of an electrostatic plotter "BENSON-9424" (a product of Benson, Inc., U.S.A.); as a result, a clear image was obtained. The cyan concentration of the printed image area of the image was 1.27.
  • Example 2 Using the same developer as in Example 1, there was made development by means of a wet copier (electrophotographic type) "DT-750" (a product of Ricoh Co., Ltd.); as a result, a clear image was obtained. The cyan concentration of the printed image area of the image was 1.19.

Landscapes

  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Liquid Developers In Electrophotography (AREA)

Claims (13)

  1. Flüssiger Entwickler für elektrostatische latente Bilder, umfassend die folgenden Bestandteile (a), (b) und (c), die in einem elektrisch Widerstandsfähigen aliphatischen Kohlenwasserstoff-Lösungsmittel mit einem spezifischen elektrischen Widerstand von nicht Weniger als 10⁹ Ωcm, einer Dielektrizitätskonstante von nicht mehr als 3 und einem Siedepunkt im Bereich von 68° bis 250°C dispergiert sind:
    (a) ein Nicht-Gel-Copolymer, das als ganzes im genannten Lösungsmittel unlöslich ist und das im wesentlichen aus 25 bis 60 Gew.-% eines Copolymersegments, das im genannten Lösungsmittel löslich ist, und aus 75 bis 40 Gew.-% eines Polymersegments besteht, das im genannten Lösungsmittel unlöslich ist, wobei das genannte lösungsmittellösliche Copolymersegment als Haupt-Monomerbestandteile (i) zumindest ein Monomer ausgewählt aus der Gruppe bestehend aus Alkylacrylaten und Alkylmethacrylaten und (ii) zumindest ein Monomer ausgewählt aus der Gruppe bestehend aus Cycloalkylmethacrylaten und Aralkylmethacrylaten enthält; und wobei das genannte lösungsmittelunlösliche Polymersegment Vinylacetat als Haupt-Monomerbestandteil enthält;
    (b) einen Farbstoff; und
    (c) ein Dispergiermittel.
  2. Flüssiger Entwickler nach Anspruch 1, worin das genannte aliphatische Kohlenwasserstoff-Lösungsmittel einen Siedepunkt im Bereich von 100° bis 200°C aufweist.
  3. Flüssiger Entwickler nach einem der vorhergehenden Ansprüche, worin das genannte Nicht-Gel-Copolymer, das als ganzes im genannten Lösungsmittel unlöslich ist, ein durchschnittliches Molekulargewicht im Bereich von 5.000 bis 50.000 aufweist.
  4. Flüssiger Entwickler nach einem der vorhergehenden Ansprüche, worin das genannte lösungsmittellösliche Copolymer-Segment im wesentlichen die in Anspruch 1 angeführten Monomerbestandteile (i) und (ii) aufweist, wobei eine weitere (iii) Vinylverbindung zugegeben ist, wobei die genannten Bestandteile (i), (ii) und (iii) jeweils in Anteilen von 40-80 Gew.-%, 20 bis 60 Gew.-% und bis zu 20 Gew.-% vorliegen.
  5. Flüssiger Entwickler nach einem der Ansprüche 1 bis 3, worin die Monomerbestandteile des genannten lösungsmittellöslichen Copolymer-Segments im wesentlichen aus
    (i) zumindest einem Monomer ausgewählt aus der Gruppe bestehend aus Alkylacrylaten und Alkylmethycrylaten; und
    (ii) zumindest einem Cycloalkylmethacrylat bestehen.
  6. Flüssiger Entwickler nach einem der vorhergehenden Ansprüche, worin die Alkylgruppe im genannten Betandteil (i) 3 bis 20 Kohlenstoffatome aufweist.
  7. Flüssiger Entwickler nach einem der vorhergehenden Ansprüche, worin der genannte Bestandteil (ii) Cyclohexylmethacrylat ist.
  8. Flüssiger Entwickler nach einem der Ansprüche 1 bis 6, worin der genannte Bestandteil (ii) Benzylmethacrylat ist.
  9. Flüssiger Entwickler nach einem der vorhergehenden Ansprüche, worin der Vinylacetat-Gehalt des genannten lösungsmittelunlöslichen Polymersegments im Bereich von 50 bis 100 Gew.-% liegt.
  10. Flüssiger Entwickler nach Anspruch 9, worin das genannte lösungsmittelunlösliche Polymersegment ein Copolymer von Vinylacetat mit zumindest einem Monomer ausgewählt aus Alkylacrylaten und Alkylmethacrylaten ist, wobei der Vinylacetat-Gehalt nicht weniger als 50 Gew.-% beträgt.
  11. Flüssiger Entwickler nach Anspruch 10, worin die Alkylgruppe der genannten Alkylacrylate oder Alkylmethacrylate 1 bis 20 Kohlenstoffatome aufweist.
  12. Flüssiger Entwickler nach einem der vorhergehenden Ansprüche, worin das genannte Dispergiermittel zumindest ein Mitglied ausgewählt aus der Gruppe bestehend aus Metallnaphthenaten, Metalloctylaten und Metallstearaten ist.
  13. Verwendung des flüssigen Entwicklers nach einem der Ansprüche 1 bis 12 zum Mehrfarbendruck.
EP86304361A 1985-06-13 1986-06-09 Flüssiger Entwickler für elektrostatische latente Bilder Expired - Lifetime EP0206606B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP127156/85 1985-06-13
JP12715685 1985-06-13

Publications (3)

Publication Number Publication Date
EP0206606A2 EP0206606A2 (de) 1986-12-30
EP0206606A3 EP0206606A3 (en) 1988-07-20
EP0206606B1 true EP0206606B1 (de) 1994-04-13

Family

ID=14953018

Family Applications (1)

Application Number Title Priority Date Filing Date
EP86304361A Expired - Lifetime EP0206606B1 (de) 1985-06-13 1986-06-09 Flüssiger Entwickler für elektrostatische latente Bilder

Country Status (4)

Country Link
US (1) US4818657A (de)
EP (1) EP0206606B1 (de)
JP (1) JPS6289971A (de)
DE (1) DE3689780T2 (de)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6289971A (ja) * 1985-06-13 1987-04-24 Toray Ind Inc 静電潜像用液体現像剤
US4837102A (en) * 1986-09-09 1989-06-06 Fuji Photo Film Co., Ltd. Liquid developer for electrostatic photography
US5055370A (en) * 1988-09-12 1991-10-08 Fuji Photo Film Co., Ltd. Image forming resin particles for liquid developer for printing plate
JP2592954B2 (ja) * 1989-03-22 1997-03-19 富士写真フイルム株式会社 湿式静電写真転写方法
US5204207A (en) * 1990-06-18 1993-04-20 Ricoh Company, Ltd. Magenta color liquid developer for electrophotography
US6255363B1 (en) 1995-09-29 2001-07-03 3M Innovative Properties Company Liquid inks using a gel organosol
JP4087444B2 (ja) * 1995-09-29 2008-05-21 スリーエム カンパニー 制御された結晶性オルガノゾルを使用する液体インク
US5652282A (en) * 1995-09-29 1997-07-29 Minnesota Mining And Manufacturing Company Liquid inks using a gel organosol
US6103781A (en) * 1996-09-26 2000-08-15 3M Innovative Properties Company Liquid inks using a controlled crystallinity organosol
US5744269A (en) * 1996-11-25 1998-04-28 Specialty Toner Corporation Method for protecting developed electrostatic images using an amphipathic toner
US7365166B2 (en) * 1997-04-07 2008-04-29 Genentech, Inc. Anti-VEGF antibodies
DE69829891T2 (de) * 1997-04-07 2005-10-06 Genentech, Inc., South San Francisco Anti-VEGF Antikörper
US20020032315A1 (en) * 1997-08-06 2002-03-14 Manuel Baca Anti-vegf antibodies
US6824489B2 (en) 1998-08-29 2004-11-30 Ina-Schaeffler Kg Differential for a motor vehicle
US7098265B2 (en) * 2000-12-29 2006-08-29 Samsung Electronics Co., Ltd. Liquid inks comprising a stable organosol
JP2012123217A (ja) * 2010-12-09 2012-06-28 Sanyo Chem Ind Ltd 電子写真用液体現像液

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3554946A (en) * 1966-11-21 1971-01-12 Ricoh Kk Liquid developers for electrophotography containing a pigment coated with a copolymer
JPS4829071B1 (de) * 1970-01-24 1973-09-06
US3900412A (en) * 1970-01-30 1975-08-19 Hunt Chem Corp Philip A Liquid toners with an amphipathic graft type polymeric molecule
GB1352067A (en) * 1971-03-18 1974-05-15 Hunt Chem Corp Philip A Liquid toners
JPS58122557A (ja) * 1982-01-18 1983-07-21 Dainippon Ink & Chem Inc 電子写真用液体現像剤
JPS61208057A (ja) * 1985-03-12 1986-09-16 Nippon Carbide Ind Co Ltd 電子写真現像剤用樹脂分散液
JPS6289971A (ja) * 1985-06-13 1987-04-24 Toray Ind Inc 静電潜像用液体現像剤

Also Published As

Publication number Publication date
JPS6289971A (ja) 1987-04-24
DE3689780D1 (de) 1994-05-19
EP0206606A2 (de) 1986-12-30
US4818657A (en) 1989-04-04
EP0206606A3 (en) 1988-07-20
DE3689780T2 (de) 1994-09-08

Similar Documents

Publication Publication Date Title
EP0206606B1 (de) Flüssiger Entwickler für elektrostatische latente Bilder
US4760009A (en) Process for preparation of liquid toner for electrostatic imaging
JP2786856B2 (ja) 電子写真用現像剤
EP0155788B1 (de) Flüssige Entwickler für elektrostatische Photographie
DE60128536T2 (de) Organosols und und diese enthaltende flüssige Tinten
JP2000206738A (ja) 電子写真現像剤及び記録材料
DE3624209C2 (de)
US4840865A (en) Liquid developer for electrostatic photography
US4789616A (en) Processes for liquid developer compositions with high transfer efficiencies
EP0156494B1 (de) Flüssigentwickler für die elektrostatische Photographie
US5204207A (en) Magenta color liquid developer for electrophotography
US4497886A (en) Electrophotographic liquid developer for the reversal development _of negatively-charged images
EP0430553A1 (de) Toner für totale Farbentwicklung
US4634651A (en) Non-aqueous type resin and electrophotographic developer containing the same
US5374495A (en) Developer for electrostatic electrophotography
KR100520925B1 (ko) 액체 잉크 조성물 및 그 제조 방법
JP3077184B2 (ja) 静電潜像現像用湿式現像剤
US4960667A (en) Positively charged black liquid electrophotographic developer compositions
US4618558A (en) Liquid developer for use in electrostatic photography
JP2720431B2 (ja) 電子写真用液体現像剤
JPH0519538A (ja) 静電荷現像用イエロー液体現像剤
JP3081637B2 (ja) 静電写真用カラー液体現像剤
JPH0251180B2 (de)
JPH08272152A (ja) 負電気的液体現像剤
JPH10260557A (ja) 静電荷現像用液体現像剤

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

AK Designated contracting states

Kind code of ref document: A2

Designated state(s): DE FR GB

PUAL Search report despatched

Free format text: ORIGINAL CODE: 0009013

AK Designated contracting states

Kind code of ref document: A3

Designated state(s): DE FR GB

17P Request for examination filed

Effective date: 19880930

17Q First examination report despatched

Effective date: 19910318

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): DE FR GB

REF Corresponds to:

Ref document number: 3689780

Country of ref document: DE

Date of ref document: 19940519

ET Fr: translation filed
PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT

26N No opposition filed
PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: DE

Payment date: 20000605

Year of fee payment: 15

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: GB

Payment date: 20000607

Year of fee payment: 15

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: FR

Payment date: 20000612

Year of fee payment: 15

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GB

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20010609

GBPC Gb: european patent ceased through non-payment of renewal fee

Effective date: 20010609

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: FR

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20020228

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: DE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20020403